Ethanethiol → HCID 22907024, compound

Participants

Reaction Steps

The AlCl3 (7 g, 52 mmol) was stirred in 150 mL of DCE at 0° C., ethanethiol (5.5 mL, 75 mmol) was added, and the mixture stirred for 15 min. The 2-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-methylpyridine (2.7 g, 7.5 mmol) in 50 mL DCE was added dropwise to the reaction mixture and stirred for 2 h as it was allowed to come to rt, then quenched with 25 mL THF at 0° C., followed by 25 mL 1N HCl and worked up. The crude product was recrystallised from hot EtOAc/ pet. ether to give 0.9 g (34 % yield) of white solid: mp 155°-157° C.; 1H NMR (CDCl3) d 2.37 (s, 6H, NCH3), 2.62 (s, 3H, pyr-CH3), 2.78-2.81 (t, 2H, J=5 Hz, CH2N), 4.05-4.07 (t, 2H, J=5 Hz, OCH2), 6.64-6.69 (m, 4H, ArH), 6.94-6.96 (d, 2H, J=8 Hz, ArH), 7.09-7.12 (d, 1H, J=8 Hz, ArH), 7.24-7.27 (comp, 2H, ArH), 7.52-7.55 (d, 1H, J=8 Hz, ArH); MS(FD) 348 (M+). Anal. Calcd for C22H24 N2O2 : C, 75.84; H, 6.94; N, 8.04. Found: C, 75.70; H, 6.98; N, 8.00.

Provenance & Evidence